Copolymer, and method for producing copolymer

Abstract

Provided is a polymer which has an acetylene group in a side chain, said polymer being capable of serving as a starting point for producing a polymer that can have various substituents. The present invention provides a copolymer comprising a first monomer unit 1A derived from a first monomer and a second monomer unit derived from a second monomer, wherein the first monomer unit 1A is a monomer unit having an acetylene group in a side chain.

Description

Copolymer and method for producing the copolymer

[0001] The present invention relates to a copolymer and a method for producing the copolymer.

[0002] In recent years, polymers with various functions have been in demand, and polymers into which desired substituents can be introduced depending on the application, as well as polymers that can serve as raw materials for such polymers, are in demand. For example, polymers having acetylene groups in their side chains may serve as a stepping stone for producing polymers that can have various substituents. For example, Non-Patent Document 1 describes an example of the use of an acrylic monomer having acetylene in its side chain.

[0003] Zhengyuan Zhang, Free radical polymerization of acrylates bearing acetylene for preparation of clickable polymers, Polymer, Volume 228, 16 July 2021, 123906

[0004] However, monovinylacetylene, which can be used as a raw material for polymers having acetylene groups in their side chains, has a low boiling point, is explosive, and is difficult to handle, making it difficult to obtain polymers having acetylene groups in their side chains.

[0005] The present invention has been made in view of the above circumstances, and provides a polymer having an acetylene group in a side chain, which can serve as a stepping stone for producing polymers that can have various substituents.

[0006] According to the present invention, there is provided a copolymer comprising a first monomer unit 1A derived from a first monomer and a second monomer unit derived from a second monomer, wherein the first monomer unit 1A is a monomer unit having an acetylene group in a side chain.

[0007] Various embodiments of the present invention are exemplified below. The embodiments shown below can be combined with each other. [1] A copolymer comprising a first monomer unit 1A derived from a first monomer and a second monomer unit derived from a second monomer, wherein the first monomer unit 1A is a monomer unit having an acetylene group in a side chain. [2] The copolymer according to [1], wherein the first monomer unit 1A is a unit represented by the following formula (1-A): (In formula (1-A), R １ is any one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group; R ２ , R ３ , R ４ are each independently any one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group. [3] The copolymer according to [1] or [2], wherein the copolymer has a solubility in a solvent of chloroform-d. １３ A copolymer having a peak β in the range of 190 to 220 ppm in a C-NMR spectrum.[4] The copolymer according to [3], wherein the copolymer has an allene structure in at least one of a main chain and a side chain.[5] The copolymer according to [4], wherein the copolymer further contains at least one selected from a first monomer unit 1B derived from a first monomer and a first monomer unit 1C derived from a first monomer, the first monomer unit 1B being represented by the following formula (1-B), and the first monomer unit 1C being represented by the following formula (1-C). (In formula (1-B), R １０１is any one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group; R １０２ , R １０３ , R １０４ are each independently any one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group. (In formula (1-C), R ２０１ is any one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group; R ２０３ , R ２０４ are each independently any one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group. １is hydrogen. [7] The copolymer according to any one of [1] to [6], wherein the second monomer is a monomer having a radical polymerizable group and includes at least one selected from the group consisting of a styrene-based monomer, a (meth)acrylic monomer, a diene-based monomer, a vinyl ether-based monomer, and an unsaturated nitrile-based monomer. [8] The copolymer according to any one of [1] to [7], wherein a content of the first monomer units 1A is 1 to 99 mol % relative to a total of 100 mol % of the first monomer units derived from the first monomer contained in the copolymer, the second monomer units, and other monomer units. [9] The copolymer according to any one of [1] to [8], wherein a single glass transition is observed in a differential scanning calorimetry curve of the copolymer, and the glass transition temperature of the copolymer is Tp±10% [K], where Tp [K] is the theoretical glass transition temperature of the copolymer, and the copolymer is composed of monomer units derived from n types of monomers, and Tp [K] satisfies the following formula (1), where T1 [K] is the glass transition temperature of a homopolymer of a first monomer, C1 is the mass fraction of the copolymerized amount of the first monomer unit relative to 100 parts by mass of the copolymer, T2 [K] is the glass transition temperature of a homopolymer of a second monomer, C2 is the mass fraction of the copolymerized amount of the second monomer unit relative to 100 parts by mass of the copolymer, Tk [K] is the glass transition temperature of a homopolymer of a k-th monomer, and Ck is the mass fraction of the copolymerized amount of the k-th monomer unit relative to 100 parts by mass of the copolymer:

[10] The copolymer according to any one of [1] to [9], which is a raw material for a Huisgen reaction with an azide compound.

[11] A method for producing a copolymer, comprising a polymerization step, in which raw material monomers including a first monomer and a second monomer are copolymerized to obtain the copolymer including first monomer units 1A derived from the first monomer and second monomer units derived from the second monomer, the first monomer units 1A being monomer units having an acetylene group in a side chain.

[12] The method for producing the copolymer according to

[11] , in which the first monomer is represented by the following formula (2): (In formula (2), R １is any one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group; R ２ , R ３ , R ４ are each independently any one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group.)

[13] A method for producing a copolymer according to

[11] or

[12] , wherein the second monomer is a monomer having a radical polymerizable group and includes at least one selected from the group consisting of a styrene-based monomer, a (meth)acrylic-based monomer, a diene-based monomer, a vinyl ether-based monomer, and an unsaturated nitrile-based monomer.

[0008] The copolymer according to the present invention can be used as a starting point for producing polymers that can have various substituents. For example, by using the copolymer according to the present invention as a raw material and carrying out a Huisgen reaction with an azide compound, a polymer having a desired amount of triazole rings with desired substituents can be obtained.

[0009] FIG. 1 shows the copolymer of Example 10. １３ FIG. 1 shows a C-NMR spectrum. FIG. 2 shows a differential scanning calorimetry curve of the copolymer according to Example 10. FIG. 3 shows an IR spectrum of the copolymer according to Example 10. FIG. 4 shows a differential scanning calorimetry curve of the copolymer according to Example 11. FIG. 5 shows a differential scanning calorimetry curve of the copolymer according to Example 12.

[0010] The present invention will be described in detail below by illustrating embodiments of the present invention. The present invention is not limited by these descriptions. The features of the embodiments of the present invention described below can be combined with each other. Furthermore, each feature can be an invention independently. Any number of "0"s (for example, one or two) may be added to the end of the numerical values ​​disclosed in the following description. For example, one or two "0"s may be added after "1.4" to make it "1.40" or "1.400".

[0011] 1. Copolymer A copolymer according to one embodiment of the present invention includes a first monomer unit 1A derived from a first monomer and a second monomer unit 1A derived from a second monomer.

[0012] 1.1 First Monomer Unit In the present invention, a monomer unit derived from a first monomer is referred to as a first monomer unit. In this specification, the term "first monomer unit" refers to a concept that includes all monomer units derived from the first monomer, and first monomer unit 1A, and the first monomer unit 1B and first monomer unit 1C described below, refer to this subordinate concept. The copolymer according to the present invention contains first monomer unit 1A. 1.1.1 First Monomer Unit 1A The first monomer unit 1A is a monomer unit having an acetylene group in its side chain. The acetylene group may have a substituent. The first monomer unit 1A can be a monomer unit derived from a monomer containing a monovinylacetylene skeleton. The first monomer unit 1A can be a unit represented by the following formula (1-A):

[0013]

[0014] In formula (1-A), R １ can be any one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group. １ is preferably hydrogen. １An example where R is a substituted or unsubstituted ether group is shown below. １ is a substituted or unsubstituted ether group, R １ may contain a substituent containing an ether group (ether bond) via C, or may contain a substituent to which an ether group (ether bond) is directly bonded without via C.

[0015] Similarly, R １ is a substituted or unsubstituted mercapto group, R １ can contain a substituent containing —S— via a C, and can also contain a substituent to which —S— is directly bonded without a C.

[0016] Similarly, R １ is a substituted or unsubstituted amino group, R １ can contain a substituent containing —NH— via a C, and can also contain a substituent to which —NH— is directly bonded without via a C.

[0017] In formula (1-A), R ２ , R ３ , R ４ are each independently any one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group. ２ , R ３ , R ４ is preferably hydrogen. Specific examples of the substituted or unsubstituted mercapto group, the substituted or unsubstituted ether group, and the substituted or unsubstituted amino group include R １ It can be the same as:

[0018] Examples of the alkyl group and alkenyl group include alkyl groups and alkenyl groups having 1 to 10 carbon atoms. Examples of the aryl group include a phenyl group and a naphthyl group, and examples of the heterocyclyl group include groups in which some of the carbon atoms in an aryl group have been replaced with heteroatoms (for example, oxygen, sulfur, or nitrogen).

[0019] Examples of the substituent that the alkyl group, alkenyl group, aryl group, mercapto group, heterocyclyl group, silyl group, and ether group may have include an alkyl group, a hydroxyl group, a halogen group, an amino group, a sulfo group, a carboxyl group, a cyano group, a nitro group, and a nitrile group.

[0020] A specific example of the first monomer unit 1A is R １ , R ２ , R ３ , R ４ and each may be hydrogen. The copolymer according to one embodiment of the present invention may have an allene structure in at least one of the main chain and the side chain. That is, the copolymer according to one embodiment of the present invention may include a monomer unit having an allene structure. The monomer unit having an allene structure will be described in detail below.

[0021] 1.1.2 First Monomer Unit 1B A copolymer according to an embodiment of the present invention may further include at least one selected from a first monomer unit 1B derived from a first monomer and a first monomer unit 1C derived from a first monomer. A copolymer according to an embodiment of the present invention may include the first monomer unit 1B. The first monomer unit 1B may be a unit represented by the following formula (1-B):

[0022]

[0023] In formula (1-B), R １０１ is R １and can be any one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group. １０１ is preferably hydrogen. Specific examples of the substituted or unsubstituted mercapto group, the substituted or unsubstituted ether group, and the substituted or unsubstituted amino group include R １ It can be the same as:

[0024] In formula (1-B), R １０２ , R １０３ , R １０４ is R ２ , R ３ , R ４ and each independently represents one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group. １０２ , R １０３ , R １０４ is preferably hydrogen. Specific examples of the substituted or unsubstituted mercapto group, the substituted or unsubstituted ether group, and the substituted or unsubstituted amino group include R １ It can be the same as:

[0025] Examples of the alkyl group and alkenyl group include alkyl groups and alkenyl groups having 1 to 10 carbon atoms. Examples of the aryl group include a phenyl group and a naphthyl group, and examples of the heterocyclyl group include groups in which some of the carbon atoms in an aryl group have been replaced with heteroatoms (for example, oxygen, sulfur, or nitrogen).

[0026] Examples of the substituent that the alkyl group, alkenyl group, aryl group, mercapto group, heterocyclyl group, silyl group, and ether group may have include an alkyl group, a hydroxyl group, a halogen group, an amino group, a sulfo group, a carboxyl group, a cyano group, a nitro group, and a nitrile group.

[0027] A specific example of the first monomer unit 1B is R １０１ , R １０２ , R １０３ , R １０４ are each hydrogen.

[0028] 1.1.3 First Monomer Unit 1C The copolymer according to one embodiment of the present invention may include a first monomer unit 1C. The first monomer unit 1C may be a unit represented by the following formula (1-C):

[0029]

[0030] In formula (1-C), R ２０１ is R １ and can be any one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group. ２０１ is preferably hydrogen. Specific examples of the substituted or unsubstituted mercapto group, the substituted or unsubstituted ether group, and the substituted or unsubstituted amino group include R １ It can be the same as:

[0031] In formula (1-C), R ２０３ , R ２０４ is R ３ , R ４and each independently represents one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group. ２０３ , R ２０４ is preferably hydrogen. Specific examples of the substituted or unsubstituted mercapto group, the substituted or unsubstituted ether group, and the substituted or unsubstituted amino group include R １ It can be the same as:

[0032] Whether the copolymer according to one embodiment of the present invention has the first monomer unit 1A, the first monomer unit 1B, and / or the first monomer unit 1C can be determined, for example, by: １３ This can be confirmed by obtaining a C-NMR spectrum, specifically by the method described in the Examples. The copolymer according to one embodiment of the present invention has first monomer unit 1B and / or first monomer unit 1C in addition to first monomer unit 1A having an acetylene group in its side chain, and therefore, for example, first monomer unit 1A having an acetylene group can be used as a functionalization site for introducing a specific substituent, and first monomer unit 1B and / or first monomer unit 1C can be used as a functionalization site for introducing another substituent.

[0033] 1.2 Second Monomer Unit The second monomer can be a monomer having a radical polymerizable group. The second monomer unit can be a monomer unit different from the first monomer. The second monomer unit can be one that does not have an acetylene group in its side chain and does not have a monovinylacetylene skeleton. The second monomer preferably includes at least one selected from the group consisting of styrene-based monomers, (meth)acrylic monomers, diene-based monomers, vinyl ether-based monomers, and unsaturated nitrile-based monomers. These can be used alone or in combination. The content of the second monomer unit in the copolymer, and the ratio of the amounts of multiple second monomers when multiple types of second monomers are included, can be appropriately set depending on the desired polymer.

[0034] The styrene-based monomer unit is a unit derived from a styrene-based monomer such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, 2,4-dimethylstyrene, ethylstyrene, p-tert-butylstyrene, α-methylstyrene, and α-methyl-p-methylstyrene.

[0035] Examples of the (meth)acrylic monomer unit include acrylic acid, methacrylic acid, methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, normal propyl acrylate, normal propyl methacrylate, isopropyl acrylate, isopropyl methacrylate, normal butyl acrylate, normal butyl methacrylate, isobutyl acrylate, isobutyl methacrylate, secondary butyl acrylate, secondary butyl methacrylate, tertiary butyl acrylate, tertiary butyl methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, normal octyl acrylate, normal octyl methacrylate, isooctyl acrylate, isooctyl methacrylate, normal and units derived from (meth)acrylic monomers such as isononyl acrylate, normal nonyl methacrylate, isononyl acrylate, isononyl methacrylate, lauryl acrylate, lauryl methacrylate, stearyl acrylate, stearyl methacrylate, ethoxydiethylene glycol acrylate, ethoxydiethylene glycol methacrylate, methoxypolyethylene glycol acrylate, methoxypolyethylene glycol methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, tetrahydrofurfuryl acrylate, tetrahydrofurfuryl methacrylate, isobornyl acrylate, and isobornyl methacrylate. Note that the term "(meth)acrylic monomer (unit)" refers to an acrylic monomer (unit) and a methacrylic monomer (unit).

[0036] The diene monomer unit is, for example, a unit derived from a conjugated diene monomer such as 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, or chloroprene.

[0037] The vinyl ether monomer unit is, for example, a unit derived from a vinyl ether monomer such as vinyl acetate, vinyl propionate, 2-hydroxyethyl vinyl ether, diethylene glycol monovinyl ether, 4-hydroxybutyl vinyl ether, vinyl methyl ether, vinyl butyl ether, and vinyl octyl ether.

[0038] The unsaturated nitrile monomer unit is a unit derived from an unsaturated nitrile monomer such as acrylonitrile, methacrylonitrile, ethacrylonitrile, or phenylacrylonitrile.

[0039] 1.3 Amount of Each Monomer Unit Contained in the Copolymer The content of the first monomer unit in the copolymer can be appropriately set depending on the desired function of the polymer, but for example, the content of the first monomer unit can be 1 to 99 mol% relative to the total 100 mol% of the moles of each monomer unit contained in the copolymer (100 mol% total of the first monomer unit, second monomer unit, and other monomer units). The content of the first monomer unit can be, for example, 1, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or 99 mol%, or can be within a range between any two of the values ​​exemplified here. The "content of first monomer unit" referred to here can include all monomer units derived from the first monomer, specifically, can include first monomer unit 1A, first monomer unit 1B, and first monomer unit 1C, and can be the total content of first monomer unit 1A, first monomer unit 1B, and first monomer unit 1C.

[0040] Similarly, the content of the second monomer unit in the copolymer may be appropriately set depending on the desired function of the polymer, and may be, for example, 1 to 99 mol% relative to the total 100 mol% of the moles of each monomer unit contained in the copolymer (100 mol% in total of the first monomer unit, second monomer unit, and other monomer units). The content of the second monomer unit may be, for example, 1, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or 99 mol%, or may be within a range between any two of the values ​​exemplified here.

[0041] The copolymer may have a structure other than the first monomer unit and the second monomer unit. The content of structures other than the first monomer unit and the second monomer unit relative to the total 100 mol% of the moles of each monomer unit contained in the copolymer (total 100 mol% of the first monomer unit, the second monomer unit, and other monomer units) may be 50 mol% or less. The content of structures other than the first monomer unit and the second monomer unit may be, for example, 0, 5, 10, 15, 20, 25, 30, 35, 40, 45, or 50 mol%, and may be within a range between any two of the values ​​exemplified here.

[0042] The content of the first monomer units 1A in the copolymer may be appropriately set depending on the desired function of the polymer, and may be, for example, 1 to 99 mol % relative to the total 100 mol % of the moles of each monomer unit contained in the copolymer (100 mol % in total of the first monomer units, second monomer units, and other monomer units). The content of the first monomer units 1A may be, for example, 1, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or 99 mol %, or may be within a range between any two of the values ​​exemplified here.

[0043] Similarly, the content of the first monomer unit 1B in the copolymer may be set appropriately depending on the desired function of the polymer, but may be, for example, 0.01 to 30 mol% relative to 100 mol% in total of the number of moles of each monomer unit contained in the copolymer (100 mol% in total of the first monomer unit, second monomer unit, and other monomer units). The content of the first monomer unit 1B may be, for example, 0.01, 0.1, 1, 5, 10, 15, 20, 25, or 30 mol%, or may be within a range between any two of the values ​​exemplified here.

[0044] The content of the first monomer unit 1C in the copolymer may be appropriately set depending on the desired function of the polymer, and may be, for example, 0.01 to 30 mol% relative to the total 100 mol% of the moles of each monomer unit contained in the copolymer (100 mol% in total of the first monomer unit, second monomer unit, and other monomer units). The content of the first monomer unit 1C may be, for example, 0.01, 0.1, 1, 5, 10, 15, 20, 25, or 30 mol%, or may be within a range between any two of the values ​​exemplified here.

[0045] The total content of first monomer units 1B and 1C in the copolymer (the content of monomer units containing an allene structure) may be set appropriately depending on the desired function of the polymer, but may be, for example, 0.01 to 30 mol% of the total mole number of each monomer unit contained in the copolymer (100 mol% (total of first monomer units, second monomer units, and other monomer units) of first monomer units 1B and 1C). The total content of first monomer units 1B and 1C may be, for example, 0.01, 0.1, 1, 5, 10, 15, 20, 25, or 30 mol%, and may be within a range between any two of the values ​​exemplified here.

[0046] By adjusting the amount of each monomer unit, the type, number, and amount of functional groups can be changed in a polymer obtained by introducing specific functional groups into each first monomer unit. The presence or absence and content of each monomer unit can be controlled by adjusting the production conditions of the copolymer, for example, by adjusting the temperature and pressure during polymerization. For example, increasing the temperature during polymerization can increase the amount of monomer units (first monomer unit 1B and first monomer unit 1C) bonded that contain an allene structure. Furthermore, decreasing the pressure during polymerization can decrease the amount of first monomer unit 1A, first monomer unit 1B, and first monomer unit 1C bonded. The presence or absence and content of each monomer unit can be controlled, for example, by １３ In the C-NMR spectrum, the amount of each functional group can be calculated based on the presence or absence of a peak appearing at a specific peak position, the peak intensity, the peak area, the amount of each functional group, and the like. It can also be confirmed by infrared spectroscopy (IR) based on the absorption associated with each functional group. Specific examples are shown in the Examples.

[0047] 1.4 Characteristics of the Copolymer The copolymer according to one embodiment of the present invention is measured in deuterated chloroform solvent. １３In the C-NMR spectrum, a peak β may be present in the range of 190 to 220 ppm. Here, peak β may be a peak derived from an allene structure. Peak β is believed to be associated with the first monomer unit 1B and / or 1C described above. Peak β may be observed, for example, at 190, 192, 194, 196, 198, 200, 202, 204, 206, 208, 210, 212, 214, 216, 218, or 220 ppm, and may be within a range between any two of the values ​​exemplified herein. Note that multiple peaks β may be observed, and for example, two peaks (peak β1 and peak β2) may be observed. Peak β1 may be observed, for example, at 190, 192, 194, 196, 198, or 200 ppm, and may be within a range between any two of the values ​​exemplified herein. Peak β2 can be observed, for example, at 200, 202, 204, 206, 208, 210, 212, 214, 216, 218, or 220 ppm, and may be within a range between any two of the values ​​exemplified here.

[0048] The copolymer according to one embodiment of the present invention is measured in deuterated chloroform solvent. １３In the C-NMR spectrum, peak α may be present in the range of 60 to 90 ppm. Here, peak α may be a peak derived from an acetylene structure. Peak α is considered to be associated with the first monomer unit 1A described above. Peak α may be observed, for example, at 60, 62, 64, 66, 68, 70, 72, 74, 75, 76, 78, 80, 82, 84, 86, 88, or 90 ppm, or may be within a range between any two of the values ​​exemplified herein. Note that multiple peaks α may be observed, or two peaks (peak α1 and peak α2) may be observed. Peak α1 may be observed, for example, at 60, 62, 64, 66, 68, 70, 72, 74, 75, or 76 ppm, or may be within a range between any two of the values ​​exemplified herein. Peak α1 may be a peak derived from a triple-bonded carbon to which hydrogen is bonded. Peak α2 may be observed at, for example, 70, 72, 74, 75, more than 75, 76, 78, 80, 82, 84, 86, 88, or 90 ppm, or may be within a range between any two of the values ​​exemplified here. Peak α2 may be a peak based on triple bond carbon to which carbon is bonded.

[0049] Furthermore, the copolymer according to one embodiment of the present invention has a viscosity measured in a deuterated chloroform solvent. １３ In the C-NMR spectrum, the ratio of the peak intensity or area of ​​peak β to the peak intensity or area of ​​peak α is preferably 1% to 15%. The ratio of the peak intensity or area of ​​peak β to the peak intensity or area of ​​peak α can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15%, and may be within a range between any two of the values ​​exemplified here.

[0050] １３ The presence or absence of peaks in the C-NMR spectrum and their peak intensities (peak areas) can be confirmed by the methods described in the Examples or methods equivalent thereto.

[0051] The copolymer according to one embodiment of the present invention preferably exhibits a single glass transition in a differential scanning calorimetry curve obtained by subjecting the copolymer to differential scanning calorimetry (DSC).​

[0052] The observation of a single glass transition means that there is one step shift in the baseline in the differential scanning calorimetry curve obtained by differential scanning calorimetry (DSC). Furthermore, when one step shift in the baseline is observed in the differential scanning calorimetry curve, the copolymer is considered to be neither a block copolymer nor a mixture of homopolymers, but a random copolymer.

[0053] The differential scanning calorimetry curve can be obtained as described in the Examples. The glass transition temperature can be the midpoint glass transition temperature (Tmg) measured in accordance with JIS K 7121.

[0054] The glass transition temperature can be adjusted by the glass transition temperatures of the homopolymers of the first monomer, the second monomer, and the other monomers, and the blending ratios thereof. When the theoretical glass transition temperature of the copolymer is Tp [K], the glass transition temperature of the copolymer is preferably Tp±10% [K] (i.e., Tp±0.1×Tp [K]). Here, when a copolymer is composed of monomer units derived from n types of monomers, Tp [K] can be such that the following formula (1) is satisfied when T1 [K] is the glass transition temperature of a homopolymer of a first monomer, C1 is the mass fraction of the copolymerization amount of the first monomer unit relative to 100 parts by mass of the copolymer, T2 [K] is the glass transition temperature of a homopolymer of a second monomer, C2 is the mass fraction of the copolymerization amount of the second monomer unit relative to 100 parts by mass of the copolymer, Tk [K] is the glass transition temperature of a homopolymer of a kth monomer, and Ck is the mass fraction of the copolymerization amount of the kth monomer unit relative to 100 parts by mass of the copolymer. n can be an integer of 2 or greater. Furthermore, C1 + C2 + ... + Cn = 1. The above formula is based on the FOX formula. The glass transition temperature is, for example, -100, -90, -80, -70, -60, -50, -40, -30, -20, -10, 0, 10, 20, 30, 35, 40, 45, 50, 55, 60, 65, 70, 80, 90, or 100°C, and may be within a range between any two of the values ​​exemplified here. A copolymer satisfying the above requirements for glass transition temperature can be obtained by adjusting the copolymer production method, particularly the type and amount of each raw material monomer, and the polymerization conditions.

[0055] The copolymer according to one embodiment of the present invention may be a random copolymer, an alternating copolymer, a block copolymer, a graft copolymer, etc. The copolymer according to one embodiment of the present invention may be a random copolymer, and the fact that it is a random copolymer can be confirmed by the observation of a single glass transition between the glass transition temperatures of the homopolymers constituting the copolymer in a differential scanning calorimetry curve. When the copolymer is composed of a first monomer unit and a second monomer unit, the fact that it is a random copolymer can be confirmed by the observation of a single glass transition between the glass transition temperature of the homopolymer of the first monomer and the glass transition temperature of the homopolymer of the second monomer.

[0056] The weight-average molecular weight of the copolymer according to one embodiment of the present invention can be 1,000 to 2,000,000. The weight-average molecular weight of the copolymer can be, for example, 1,000, 5,000, 10,000, 50,000, 100,000, 500,000, 1,000,000, or 2,000,000, and may be within a range between any two of the values ​​exemplified here. The weight-average molecular weight can be a polystyrene-equivalent value measured by gel permeation chromatography (GPC), and can be, for example, a value measured under the measurement conditions described below. Apparatus name: HLC-8320 (manufactured by Tosoh Corporation); Column: Three TSKgel GMHHR-H columns in series; Temperature: 40°C; Detection: Differential refractive index; Solvent: Tetrahydrofuran; Calibration curve: Can be prepared using standard polystyrene (PS).

[0057] The copolymer according to one embodiment of the present invention can be a starting point for producing a polymer that can have various substituents. For example, the copolymer according to one embodiment of the present invention can be used as a raw material for the Huisgen reaction with an azide-based compound. For example, the copolymer according to one embodiment of the present invention can be used as a starting material for the Huisgen reaction with an azide-based compound having a substituent R (R-N ３ ) and a compound having a triazole ring with a substituent R can be obtained by the Huisgen reaction, and the target compound can be obtained with high efficiency and high accuracy while suppressing the amount of by-products produced.

[0058] 2. Method for Producing a Copolymer According to one embodiment of the present invention, a method for producing a copolymer includes a polymerization step in which raw material monomers including a first monomer and a second monomer are copolymerized to obtain a copolymer. The first monomer unit 1A has an acetylene group in a side chain.

[0059] 2.1 First Monomer The first monomer can be represented by the following formula (2):

[0060] R in the above formula (2) １ , R ２ , R ３ and R ４ is the same as in the above formula (1-A). １ , R ２ , R ３ and R ４ is R in formula (1-B) １０１ , R １０２ , R １０３ , R １０４ The same can be said as R in the above formula (2). １ , R ３ and R ４ is R in formula (1-C) ２０１ , R ２０３ , R ２０４ It can be the same as:

[0061] 2.2 Second Monomer The second monomer may be a monomer having a radical polymerizable group. The second monomer preferably includes at least one selected from the group consisting of a styrene-based monomer, a (meth)acrylic-based monomer, a diene-based monomer, a vinyl ether-based monomer, and an unsaturated nitrile-based monomer. These may be used alone or in combination.

[0062] Examples of the styrene-based monomer include styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, 2,4-dimethylstyrene, ethylstyrene, p-tert-butylstyrene, α-methylstyrene, and α-methyl-p-methylstyrene.

[0063] Examples of the (meth)acrylic monomer include acrylic acid, methacrylic acid, methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, normal propyl acrylate, normal propyl methacrylate, isopropyl acrylate, isopropyl methacrylate, normal butyl acrylate, normal butyl methacrylate, isobutyl acrylate, isobutyl methacrylate, secondary butyl acrylate, secondary butyl methacrylate, tertiary butyl acrylate, tertiary butyl methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, normal octyl acrylate, normal octyl methacrylate, isooctyl acrylate, and isooctyl methacrylate. (Meth)acrylic monomers such as normal nonyl acrylate, normal nonyl methacrylate, isononyl acrylate, isononyl methacrylate, lauryl acrylate, lauryl methacrylate, stearyl acrylate, stearyl methacrylate, ethoxydiethylene glycol acrylate, ethoxydiethylene glycol methacrylate, methoxypolyethylene glycol acrylate, methoxypolyethylene glycol methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, tetrahydrofurfuryl acrylate, tetrahydrofurfuryl methacrylate, isobornyl acrylate, and isobornyl methacrylate. Note that the term "(meth)acrylic monomer (unit)" refers to an acrylic monomer (unit) and a methacrylic monomer (unit).

[0064] The diene monomer is, for example, a unit derived from a conjugated diene monomer such as 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, or chloroprene.

[0065] Examples of the vinyl ether monomer include vinyl acetate, vinyl propionate, 2-hydroxyethyl vinyl ether, diethylene glycol monovinyl ether, 4-hydroxybutyl vinyl ether, vinyl methyl ether, vinyl butyl ether, and vinyl octyl ether.

[0066] The unsaturated nitrile monomer is an unsaturated nitrile monomer such as acrylonitrile, methacrylonitrile, ethacrylonitrile, or phenylacrylonitrile.

[0067] 2.3 Charge Amounts of First Monomer and Second Monomer, etc. In a polymerization process according to one embodiment of the present invention, the charge amount of the first monomer can be 1 to 99 parts by mass when the total amount of the raw material monomers used in the polymerization process is 100 parts by mass. The charge amount of the first monomer can be, for example, 1, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or 99 parts by mass, or can be within a range between any two of the values ​​exemplified here. In a polymerization process according to one embodiment of the present invention, the charge amount of the second monomer can be 1 to 99 parts by mass when the total amount of the raw material monomers used in the polymerization process is 100 parts by mass. The amount of the second monomer may be, for example, 1, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or 99 parts by mass, or may be within a range between any two of the numerical values ​​exemplified herein. In the polymerization step according to one embodiment of the present invention, when the total amount of the raw material monomers used in the polymerization step is 100 parts by mass, the amount of monomers other than the first monomer and the second monomer may be 50 parts by mass or less. For example, the amount may be 0, 5, 10, 15, 20, 25, 30, 35, 40, 45, or 50 parts by mass, or may be within a range between any two of the numerical values ​​exemplified herein.

[0068] The polymerization step can be radical polymerization of the first monomer and the second monomer using an initiator. The polymerization initiator is not particularly limited, but examples thereof include azo compounds such as azobisisobutyronitrile, azobiscyclohexanecarbonitrile, azobismethylpropionitrile, and azobismethylbutyronitrile, and organic peroxides such as benzoyl peroxide, t-butylperoxybenzoate, 1,1-bis(t-butylperoxy)-3,3,5-trimethylcyclohexane, t-butylperoxyisopropyl monocarbonate, t-butylperoxy-2-ethylhexanoate, di-t-butyl peroxide, dicumyl peroxide, ethyl-3,3-di-(t-butylperoxy)butyrate, and 1,1,3,3-tetramethylbutoxyperoxy-2-ethylhexanoate. These initiators may be used alone or in combination. The amount of the polymerization initiator used is not particularly limited, but may be, for example, 0.0, 0.2, 0.3, 0.4, 0.5, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0, 4.5, or 5.0 mol% relative to 100 mol% of all monomer units, and may be within a range between any two of the numerical values ​​exemplified here.

[0069] A chain transfer agent can be used in the polymerization step. Examples of the chain transfer agent include, but are not limited to, n-octyl mercaptan, n-dodecyl mercaptan, t-dodecyl mercaptan, α-methylstyrene dimer, ethyl thioglycolate, limonene, and terpinolene. The amount of the chain transfer agent used is not particularly limited as long as it is within a range in which the target molecular weight can be obtained. For example, the amount of the chain transfer agent used is 0.01, 0.02, 0.03, 0.04, 0.05, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, or 2.0 mol% relative to 100 mol% of all monomer units, and may be within a range between any two of the values ​​exemplified here.

[0070] In the polymerization process, first, the second monomer, initiator, and chain transfer agent are added to a solvent, and the gas phase is replaced with an inert gas such as nitrogen. The first monomer is then pumped with the inert gas and heated under pressure to polymerize. The polymerization conditions can be adjusted depending on the type of raw material monomer and the desired polymer properties. For example, the pressure can be 0.005 to 0.050 MPaG. The pressure can be, for example, 0.005, 0.010, 0.015, 0.020, 0.025, 0.030, 0.035, 0.040, 0.045, or 0.050 MPaG, or can be within a range between any two of the values ​​exemplified here. The temperature can be, for example, 40 to 100°C. The temperature is, for example, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or 100°C, and may be within a range between any two of the values ​​exemplified here. When the copolymer contains first monomer units 1B and / or 1C, an example of preferred production conditions includes a polymerization temperature of 80°C and a pressure of 0.15 MPaG or higher. In the polymerization step, polymerization can be carried out until the polymerization rate reaches 5 to 50%.

[0071] The present invention will be described in more detail below based on examples, but the present invention should not be construed as being limited to these examples.

[0072] Example 1: A 1000 ml glass pressure vessel was charged with 400 ml of tetrahydrofuran, 208.3 g of styrene monomer, 1.1 g of dodecyl mercaptan, and 1.6 g of 1,1,3,3-tetramethylbutoxyperoxy-2-ethylhexanoate (Perocta O, manufactured by NOF Corporation), and the gas phase was replaced with nitrogen. 43.7 g of monovinylacetylene (MVA) was pumped using nitrogen and pressurized to 0.01 MPaG. The reaction solution was heated to 70°C and reacted until a polymerization rate of 30% was reached. After cooling, the reaction solution and methanol were mixed to obtain a copolymer. The polymerization rate indicates the mass% of the obtained copolymer when the charged first monomer and second monomer are taken as 100 mass%. The number average molecular weight Mn of the obtained copolymer was 6,608, and the weight average molecular weight Mw was 11,930. The number average molecular weight Mn and weight average molecular weight Mw were analyzed by gel permeation chromatography (GPC) under the following measurement conditions: Apparatus name: HLC-8320 (manufactured by Tosoh Corporation) Column: Three TSKgel GMHHR-H columns in series Temperature: 40°C Detection: Differential refractive index Solvent: Tetrahydrofuran Calibration curve: Prepared using standard polystyrene (PS).

[0073] Examples 2 to 9 Copolymers were obtained in the same manner as in Example 1, except that the types and amounts of the first and second monomers and the polymerization conditions were as shown in Table 1.

[0074] The resulting copolymer １３ The copolymer was analyzed by C-NMR to determine the content of the first monomer unit 1A. The content of the first monomer unit 1A indicates the content of the first monomer unit 1A when the total of all monomer units contained in the copolymer is taken as 100 mol % (i.e., when the total of the first monomer units 1A, 1B, and 1C and the second monomer unit is taken as 100 mol %). １３ Measurement was carried out by C-NMR under the following conditions: Apparatus name: FT-NMR AVANCE300 (manufactured by BRUKER) Solvent: deuterated chloroform Concentration: 6.25% by mass Temperature: 27°C Number of accumulations: 8000

[0075] The copolymer obtained was subjected to differential scanning calorimetry (DSC) to determine the midpoint glass transition temperature (Tmg) in accordance with JIS K 7121. The measurement conditions are as follows: Measurement equipment: Seiko Electronics EXSTAR6000 DSC-6200 Amount of sample measured: 10 mg Temperature increase / decrease: Cool from 25°C to -80°C at 10°C / min, hold at -80°C for 10 minutes, increase temperature from -80°C to 150°C at a rate of 10°C / min Measurement atmosphere: Nitrogen

[0076]

[0077] Example 10: A 1000 ml glass pressure vessel was charged with cyclopentyl methyl ether (CPME), 208.3 g of styrene monomer, and 1.6 g of 1,1,3,3-tetramethylbutoxyperoxy-2-ethylhexanoate (Perocta O, manufactured by NOF Corporation), and the gas phase was replaced with nitrogen. 43.7 g of monovinyl acetylene (MVA) was pumped using nitrogen and pressurized to 0.01 MPaG. The reaction solution was heated to 70°C and reacted until the polymerization rate reached 100%. After cooling, the reaction solution and methanol were mixed to obtain a copolymer. Furthermore, the number average molecular weight Mn and polydispersity index PDI (Mw / Mn) were determined by gel permeation chromatography (GPC) in the same manner as in Example 1, and the results are shown in Table 2.

[0078] Examples 11 and 12 Copolymers were obtained in the same manner as in Example 10, except that the types and amounts of the first and second monomers and the polymerization conditions were as shown in Table 2.

[0079] The copolymer of Example 10 was subjected to the same procedure as in Example 1. １３ The obtained product was analyzed by C-NMR. １３ The C-NMR spectrum is shown in Figure 1. As shown in Figure 1, two peaks were confirmed in the range of 190 to 220 ppm (near 205 ppm (intensity 0.0300) and near 192 ppm (intensity 0.0029)). In addition, peaks were confirmed near 88 ppm (intensity 0.4166) and near 70 ppm (intensity 0.4201).

[0080] Differential scanning calorimetry (DSC) was performed on the copolymers according to Examples 10 to 12 in the same manner as in Example 1, and differential scanning calorimetry curves were obtained. The midpoint glass transition temperature (Tmg, hereinafter also referred to as Tg) was calculated in accordance with JIS K 7121. The differential scanning calorimetry curves are shown in Figure 2 (Example 10), Figure 4 (Example 11), and Figure 5 (Example 12). In each differential scanning calorimetry curve, a single glass transition was observed between 40 and 60°C. It was also confirmed that the glass transition temperature could be controlled by changing the type and ratio of the components blended. Furthermore, assuming that the Tg of polystyrene was 100°C (373.15K), the Tg of polymonovinylacetylene was estimated using the Fox equation from the Tg of the copolymer according to Example 10 (58.81°C (331.96K)), resulting in a value of -57.8°C (215.35K). Furthermore, when the Tg of polymethyl methacrylate was set to 105°C and the Tg of polymonovinylacetylene was set to -57.8°C, the Tp of Examples 11 and 12 was calculated. The Tg of the copolymers according to Examples 11 and 12 was within Tp of the copolymers according to Examples 11 and 12 ±10% [K].

[0081] The IR spectrum of the copolymer of Example 10 was obtained by infrared spectroscopy (IR). The results are shown in Figure 3. As shown in Figure 3, －１ An absorption peak thought to be due to the acetylene group was confirmed around 4000 cm. The measurement conditions are as follows: Measurement equipment: Perkin Elmer FT-IR Spectrometer Frontier Detector: ST Janan Durascope Focusing lens: KRS-5 Measurement method: Single reflection ATR method Measurement start: 4000 cm －１ End of measurement: 400 cm －１ Resolution: 4cm －１ Number of times: 16 Interval: 1.0 cm －１

[0082]

[0083] (Example 1-2 (same conditions as Example 10)) Cyclopentyl methyl ether (CPME), 208.3 g of styrene monomer, and 1.6 g of 1,1,3,3-tetramethylbutoxyperoxy-2-ethylhexanoate (Perocta O, manufactured by NOF Corporation) were charged into a 1000 ml glass pressure vessel, and the gas phase was replaced with nitrogen. 43.7 g of monovinylacetylene (MVA) was pumped in using nitrogen, and the pressure was increased to 0.01 MPaG. The reaction solution was heated to 70°C, and the reaction was carried out until the polymerization rate reached 100%. After cooling, the reaction solution and methanol were mixed to obtain a copolymer.

[0084] Examples 2-2 to 5-2, 9-2 Copolymers were obtained in the same manner as in Example 1-2, except that the types and amounts of the first and second monomers and the polymerization conditions were as shown in Table 3.

[0085] (Example 6-2) A 1000 ml glass pressure vessel was charged with cyclopentyl methyl ether (CPME), 208.3 g of chloroprene monomer, 1.1 g of dodecyl mercaptan, and 1.6 g of 1,1,3,3-tetramethylbutoxyperoxy-2-ethylhexanoate (Perocta O, manufactured by NOF Corporation), and the gas phase was replaced with nitrogen. 43.7 g of monovinyl acetylene (MVA) was pumped using nitrogen, and the pressure was increased to 0.01 MPaG. The reaction solution was heated to 70°C and reacted until the polymerization rate reached 100%. After cooling, the reaction solution was mixed with methanol to obtain a copolymer.

[0086] Examples 7-2 and 8-2 Copolymers were obtained in the same manner as in Example 6-2, except that the types and amounts of the first and second monomers and the polymerization conditions were as shown in Table 3.

[0087] The copolymers according to Examples 1-2 to 9-2 were subjected to the same procedure as in Example 1. １３ The polymer was analyzed by C-NMR to determine the content of the first monomer unit 1A. Differential scanning calorimetry (DSC) was also performed in the same manner as in Example 1 to obtain a differential scanning calorimetry curve. The midpoint glass transition temperature (Tmg) was calculated in accordance with JIS K 7121. The results are shown in Table 3.

[0088]

Claims

1. A copolymer comprising a first monomer unit 1A derived from a first monomer and a second monomer unit derived from a second monomer, wherein the first monomer unit 1A is a monomer unit having an acetylene group in a side chain.

2. The copolymer according to claim 1, wherein the first monomer unit 1A is a unit represented by the following formula (1-A): (In formula (1-A), R １ is any one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group; R ２ , R ３ , R ４ are each independently any one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group.

3. The copolymer according to claim 1 or 2, wherein the copolymer is measured in a deuterated chloroform solvent. １３ A copolymer having at least one peak β observed in the range of 190 to 220 ppm in a C-NMR spectrum.

4. The copolymer according to claim 3, wherein the copolymer has an allene structure in at least one of the main chain and the side chain.

5. The copolymer according to claim 4, further comprising at least one selected from a first monomer unit 1B derived from a first monomer and a first monomer unit 1C derived from a first monomer, wherein the first monomer unit 1B is represented by the following formula (1-B), and the first monomer unit 1C is represented by the following formula (1-C). (In formula (1-B), R １０１ is any one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group; R １０２ , R １０３ , R １０４ are each independently any one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group. (In formula (1-C), R ２０１ is any one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group; R ２０３ , R ２０４ are each independently any one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group.

6. The copolymer according to claim 2, wherein R １ is hydrogen, copolymer.

7. The copolymer according to claim 1 or 2, wherein the second monomer is a monomer having a radical polymerizable group and includes at least one selected from the group consisting of a styrene-based monomer, a (meth)acrylic-based monomer, a diene-based monomer, a vinyl ether-based monomer, and an unsaturated nitrile-based monomer.

8. The copolymer according to claim 1 or 2, wherein the content of the first monomer units 1A is 1 to 99 mol % relative to a total of 100 mol % of the first monomer units derived from the first monomer contained in the copolymer, the second monomer units, and other monomer units.

9. A copolymer according to claim 1 or 2, wherein a single glass transition is observed in a differential scanning calorimetry curve of the copolymer, wherein the glass transition temperature of the copolymer is Tp±10% [K], where Tp [K] is the theoretical glass transition temperature of the copolymer, and wherein the copolymer is composed of monomer units derived from n types of monomers, and wherein Tp [K] satisfies the following formula (1), where T1 [K] is the glass transition temperature of a homopolymer of a first monomer, C1 is the mass fraction of the copolymerized amount of the first monomer unit relative to 100 parts by mass of the copolymer, T2 [K] is the glass transition temperature of a homopolymer of a second monomer, C2 is the mass fraction of the copolymerized amount of the second monomer unit relative to 100 parts by mass of the copolymer, Tk [K] is the glass transition temperature of a homopolymer of a kth monomer, and Ck is the mass fraction of the copolymerized amount of the kth monomer unit relative to 100 parts by mass of the copolymer:

10. The copolymer according to claim 1 or 2, which is used as a raw material for the Huisgen reaction with an azide compound.

11. A method for producing a copolymer, comprising a polymerization step, in which raw material monomers including a first monomer and a second monomer are copolymerized to obtain the copolymer including first monomer units 1A derived from the first monomer and second monomer units derived from the second monomer, and the first monomer units 1A are monomer units having an acetylene group in a side chain.

12. A method for producing a copolymer according to claim 11, wherein the first monomer is represented by the following formula (2): (In formula (2), R １ is any one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group; R ２ , R ３ , R ４ are each independently any one selected from the group consisting of hydrogen, chlorine, bromine, iodine, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ether group, and a substituted or unsubstituted amino group.

13. A method for producing a copolymer according to claim 11 or 12, wherein the second monomer is a monomer having a radical polymerizable group and includes at least one selected from the group consisting of a styrene-based monomer, a (meth)acrylic-based monomer, a diene-based monomer, a vinyl ether-based monomer, and an unsaturated nitrile-based monomer.

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